Skybound Sales Internship (Chicago, IL)

Working at Goosehead

We've worked hard to earn the trust of our clients, so we are highly selective in our hiring process. If you think you have what it takes to grow with our company, we would love to meet you.

Since 2003, Goosehead Insurance has been disrupting the insurance industry by giving clients the power of choice, utilizing a smarter marketing approach, and delivering world‑class service. This is all powered by our focus on hiring and retaining extraordinary people.

Skybound is an extension of this mission – designed to identify and accelerate the next generation of high‑performing sales talent.

Principal Duties and Responsibilities

The Skybound Internship is an 8‑week, high‑intensity sales and leadership development program. Interns receive hands‑on exposure to the business through:

• Prospecting and establishing referral partner relationships alongside top‑producing Account Executives.
• Shadowing sales leaders and learning Goosehead’s proven sales process from prospecting to closing.
• Supporting producers by setting real referral partner (RP) meetings to drive business development.
• Participation in various department immersion days within the company to understand the business operations.
• Engaging in professional development workshops, training, and a final capstone project presented to leadership.

Compensation Summary

The Skybound Internship is a paid, part‑time program with on‑target earnings of $3,600 over the 8‑week duration. Compensation includes:

• Hourly pay varies by location
• 28 hours per week (Monday–Thursday)
• 8‑week program duration

Please note: Housing and relocation are not included as part of the compensation offering.

Top‑performing interns may also be considered for a full‑time Account Executive offer following graduation and a part‑time Associate Account Executive role during their senior year.

Training and Program Requirements

• Interns receive structured training in sales process management, business development, Salesforce, and Goosehead systems—no prior sales experience required.
• Interns must commit to the full 8‑week program schedule (Mon–Thu, 8:00 AM – 4:00 PM).

Professional development pathways from Skybound may include a full‑time Account Executive offer, and long‑term opportunities such as agency ownership or corporate leadership.

Benefits Summary

While interns are hourly employees and not eligible for full‑time benefits, Goosehead provides:

• Coordinated travel and experiences during program kickoff
• Hands‑on training from top producers and leaders
• Access to Goosehead systems, tools, and development resources
• Eligibility for future full‑time roles with competitive compensation and benefits

Full‑time benefits apply only if/when an intern converts to an Account Executive role.

Experience and Education

• Current college juniors
• 3.0 GPA recommended
• Demonstrated leadership, involvement, or prior work experience
• Legally authorized to work in the United States

Local candidates within the internship markets below are strongly preferred due to engagement, culture fit, and conversion potential.

• Dallas, TX
• Fort Worth, TX
• Houston, TX
• Austin, TX
• Denver, CO
• Seattle, WA
• Tempe, AZ
• Chicago, IL
• Arlington, VA
• Columbus, OH
• Charlotte, NC
• Minneapolis, MN
• Indianapolis, IN
• Nashville, TN

Preferred Skills, Abilities, Soft Skill Factors

• Exceptional written and verbal communication
• Competitive attitude and strong work ethic
• Coachable mindset and openness to feedback
• Interest in sales, business, or entrepreneurship
• Strong time management and organization
• Ability to build rapport and work collaboratively
• Problem‑solving mentality and initiative
• High integrity, professionalism, and accountability

Equal Employment Opportunity

Goosehead is an equal opportunity employer and complies with all applicable federal, state, and local laws, rules, guidelines, and regulations. Goosehead strictly prohibits and does not tolerate unlawful discrimination against employees, applicants, or any other covered person because of race, color, religion, creed, national origin, ancestry, ethnicity, sex (including pregnancy, childbirth, and related medical conditions), sexual orientation, gender, gender identity, transgender status, age, physical or mental disability, veteran status, uniformed service, genetic information, or any other characteristic protected by applicable law. All applicants for employment and all Goosehead employees are given equal consideration based solely on job‑related factors such as qualifications, experience, performance, and availability.